ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Hybridorubrins A-D: Azaphilone Heterodimers from Stromata of Hypoxylon fragiforme and Insights into the Biosynthetic Machinery for Azaphilone Diversification.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 31 citations in OpenAlex.
- From Pigment Chemistry to Nanomaterials: Fungal Pigments as Reducing and Stabilizing Agents in Green Nanoparticle Synthesis.Microorganisms · 2026Review
- Brønsted acid-catalyzed two-component tandem condensation and cycloisomerization to 6(2RSC advances · 2025Article
- Cytochalasins from the Ash Endophytic FungusMolecules (Basel, Switzerland) · 2025Article
- IMA fungus · 2025Review
- Strong antagonism of an endophyte ofApplied and environmental microbiology · 2024Article
- Biotransformation-coupled mutasynthesis for the generation of novel pristinamycin derivatives by engineering the phenylglycine residue.RSC chemical biology · 2023Article
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- Inhibitory Effects of the Fungal Pigment Rubiginosin C on Hyphal and Biofilm Formation inJournal of fungi (Basel, Switzerland) · 2023Article
- Azaphilones produced by Penicillium maximae with their cell death-inducing activity on Adriamycin-treated cancer cell.Genes and environment : the official journal of the Japanese Environmental Mutagen Society · 2023Article
- Azaphilone alkaloids: prospective source of natural food pigments.Applied microbiology and biotechnology · 2022Review
- Two New Triterpenes from Basidiomata of the Medicinal and Edible Mushroom,Molecules (Basel, Switzerland) · 2021Article
- Core Steps to the Azaphilone Family of Fungal Natural Products.Chembiochem : a European journal of chemical biology · 2021Review
- Recent Findings in Azaphilone Pigments.Journal of fungi (Basel, Switzerland) · 2021Review
- Secondary metabolite biosynthetic diversity in the fungal familyStudies in mycology · 2021Article
- Three New Derivatives of Zopfinol fromJournal of fungi (Basel, Switzerland) · 2021Article
- Hybridorubrins A-D: Azaphilone Heterodimers from Stromata of Hypoxylon fragiforme and Insights into the Biosynthetic Machinery for Azaphilone Diversification.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Biosynthesis of Antibacterial Iron-Chelating Tropolones inFrontiers in fungal biology · 2021Article
- Unsaturated Fatty Acids Control Biofilm Formation ofAntibiotics (Basel, Switzerland) · 2020Article
- Simplicilones A and B Isolated from the Endophytic FungusAntibiotics (Basel, Switzerland) · 2020Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
The diversity of azaphilones in stromatal extracts of the fungus Hypoxylon fragiforme was investigated and linked to their biosynthetic machineries by using bioinformatics. Nineteen azaphilone-type compounds were isolated and characterized by NMR spectroscopy and mass spectrometry, and their absolute stereoconfigurations were assigned by using Mosher ester analysis and electronic circular dichroism spectroscopy. Four unprecedented bis-azaphilones, named hybridorubrins A-D, were elucidated, in addition to new fragirubrins F and G and various known mitorubrin derivatives. Only the hybridorubrins, which are composed of mitorubrin and fragirubrin moieties, exhibited strong inhibition of Staphylococcus aureus biofilm formation. Analysis of the genome of H. fragiforme revealed the presence of two separate biosynthetic gene clusters (BGCs) hfaza1 and hfaza2 responsible for azaphilone formation. While the hfaza1 BGC likely encodes the assembly of the backbone and addition of fatty acid moieties to yield the (R)-configured series of fragirubrins, the hfaza2 BGC contains the necessary genes to synthesise the widely distributed (S)-mitorubrins. This study is the first example of two distant cross-acting fungal BGCs collaborating to produce two families of azaphilones and bis-azaphilones derived therefrom.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.